(Z)-Guggulsterone Chemical Properties

Melting point:

188-190°

alpha 

D26 -61° (c = 1 in chloroform)

Boiling point:

463.3±45.0 °C(Predicted)

Density 

1.10±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: 5 mg/mL

form 

powder

color 

light yellow

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.

InChI

InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4+/t15-,17+,18+,20+,21-/m1/s1

InChIKey

WDXRGPWQVHZTQJ-OSJVMJFVSA-N

SMILES

C1(=O)C=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)/C(=C/C)/C(=O)C3)CC2

LogP

3.650 (est)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37-38

Safety Statements 

36

WGK Germany 

3

HS Code 

2914299000

MSDS

• Language:English Provider:SigmaAldrich

(Z)-Guggulsterone Usage And Synthesis

Description

Guggulsterone-(Z) (39025-23-5) is a natural steroid from?Commiphora mukul?extract (guggulipid) which lowers cholesterol and acts as an FXR antagonist.1?Attenuates astrocyte-mediated neuroinflammation.2? Induces differentiation of pluripotent stem cells to dopaminergic neurons.3 Produces antidepressant-like effects via activation of the BDNF signaling pathway in mouse models.4

Uses

(Z)-Guggulsterone acts as an α-glucosidase inhibitor also known as a hypolipidemic agent.

Uses

Z-Guggulsterone acts as an α-glucosidase inhibitor also known as a hypolipidemic agent.

Definition

ChEBI: Guggulsterone is a 3-hydroxy steroid. It has a role as an androgen.

Biological Activity

Broad spectrum steroid receptor ligand; mineralocorticoid, progesterone and glucocorticoid receptor antagonist (K i values are 37, 224 and 252 nM respectively) and weak androgen receptor agonist (K i = 315 nM). Induces apoptosis in prostate cancer cells and inhibits angiogenesis via suppression of the VEGF-VEGFR2-Akt signalling pathway. Exhibits antilipidemic activity via antagonism of the farnesoid X receptor (FXR) and displays antiseptic, antirheumatic and anti-inflammatory activity in vivo . More active isomer of Guggulsterone (Pregna-4,17(20)-diene-3,16-dione ).

Biochem/physiol Actions

(Z)-Guggulsterone is a natural product that lowers cholesterol due to its function as an antagonist ligand for the bile acid receptor. (Z)-Guggulsterone is a nuclear hormone receptor that regulates the transcription of several genes involved in cholesterol metabolism and plays a role in cholesterol level regulation. (Z)-Guggulsterone is also a selective farnesoid X receptor (FXR) modulator.

storage

Store at RT

References

1) Urizar?et al.?(2002),?A Natural Product That Lowers Cholesterol as an Antagonist Ligand for FXR; Science,?296?1703 2) Liu?et al.?(2018),?Z-Guggulsterone attenuates astrocytes-mediated neuroinflammation after ischemia by inhibiting toll-like receptor 4 pathway; J. Neurochem.,?147?803 3) Agbay?et al.?(2018),?Guggulsterone-releasing Microspheres Direct the Differentiation of Human Induced Pluripotent Stem Cells Into Neural Phenotypes; Biomed. Mater.,?13?034104 4) Liu?et al.?(2017),?Z-Guggulsterone Produces Antidepressant-Like Effects in Mice through Activation of the BDNF Signaling Pathway; Int. J. Neuropsychopharmacol.,?20?485

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